Everything You Need To Know About Hugh Hefner

Here's How Hugh Hefner Went On To Fulfill The Playboy Dream

Update: Hugh Hefner died at his home, the Playboy Mansion, on September 27, 2017. R.I.P.

Based on Hugh Hefner’s upbringing, you’d think he’d have grown up to be a priest, not a playboy. The Chicago-born founded Playboy in 1953, a magazine that not only spawned the multimillion-dollar Playboy Enterprises, but that’s credited for helping usher in the sexual revolution of the 1960s. And therein lies Hefner’s true success: His ability as an editor and businessman aside, Hef has actively campaigned for everything from gay rights to freedom of speech, and he did it all while living the kind of hedonistic lifestyle most men can only dream of. A success story of the highest order.

A post shared by Hugh Hefner (@hughhefner) on May 10, 2016 at 2:15pm PDT

A a student at Chicago's Steinmetz High School in 1940, Hefner slowly emerged from his shell, discovering the pleasures of dancing and, of course, women. After high school — where he excelled at activities like journalism, drawing animation and serving as president of the student council — Hefner joined the army as a writer for the military newspaper before being honorably discharged.

There’s perhaps no better living personification of the American Dream than Hugh Hefner. Hugh Hefner has made a career of destigmatizing sex, making it as ubiquitous as cereal, or white bread. But while we spent our adolescence hiding in our bathroom transfixed by the women that graced the pages of Playboy, Hefner was in the Playboy Mansion having sex with them. All of them. All the time. Men learned to live vicariously through him. If we couldn’t do it, we’re glad someone could.

But despite the impressive pedigree, Hugh Hefner couldn’t escape the moral watchdogs who wanted his head on a stick. In 1963, they almost got it when Hefner was arrested for selling obscene literature after an issue of Playboy featuring nude shots of Jayne Mansfield was released. Fortunately the jury was unable to come to a verdict, and Hefner walked. Since then, some of the most famous women in the world have appeared in the pages of Playboy, including Drew Barrymore, Nancy Sinatra, Pamela Anderson, Suzanne Somers, and Farrah Fawcett.

There’s no denying that Playboy still has value as a global brand, and we’d all still kill to have even one drink in the Playboy Mansion, but for the past few years, Playboy just hasn't been what it used to be. Part of this has to do with growing digital technologies, which have made access to pornography easier than access to cookies in a jar on top of the fridge.

7. Hefner mortgaged his furniture to launch Playboy

He made $600 from the sale and raised $8,000 from 45 investors to launch the magazine.

8. He’s been married three times, and has 4 children

In 2012, Hefner said his youngest son, Cooper, would likely succeed him as the public face of Playboy.

9. He doesn't discriminate

In his younger years, Hefner has acknowledged experimenting with bisexuality.

10. There is an award named after him

Created by his daughter Christie Hefner, the Hugh M. Hefner First Amendment Award “honors individuals who have made significant contributions in the vital effort to protect and enhance First Amendment rights for Americans."